Benzyl alcohol
- Formula: C7H8O
- Molecular weight: 108.1378
- IUPAC Standard InChIKey: WVDDGKGOMKODPV-UHFFFAOYSA-N
- CAS Registry Number: 100-51-6
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Benzenemethanol; α-Hydroxytoluene; α-Toluenol; (Hydroxymethyl)benzene; Benzenecarbinol; Phenylcarbinol; Phenylmethanol; Phenylmethyl alcohol; Methanol, phenyl-; NCI-C06111; Hydroxytoluene; Bentalol; Benzoyl alcohol; Benzenmethanol; Benzylic alcohol; Methanol benzene; NSC 8044; Benzyl Alkohol
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -94.6 ± 3.0 | kJ/mol | Ccr | Papina, Pimenova, et al., 1995 | ALS |
ΔfH°gas | -100.7 | kJ/mol | N/A | Parks, Manchester, et al., 1954 | Value computed using ΔfHliquid° value of -161.0±1.3 kj/mol from Parks, Manchester, et al., 1954 and ΔvapH° value of 60.3 kj/mol from Papina, Pimenova, et al., 1995.; DRB |
ΔfH°gas | -113.7 | kJ/mol | N/A | Landrieu, Baylocq, et al., 1929 | Value computed using ΔfHliquid° value of -174.0 kj/mol from Landrieu, Baylocq, et al., 1929 and ΔvapH° value of 60.3 kj/mol from Papina, Pimenova, et al., 1995.; DRB |
ΔfH°gas | -106.7 | kJ/mol | N/A | Schmidlin, 1906 | Value computed using ΔfHliquid° value of -167.0 kj/mol from Schmidlin, 1906 and ΔvapH° value of 60.3 kj/mol from Papina, Pimenova, et al., 1995.; DRB |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -154.9 ± 3.0 | kJ/mol | Ccr | Papina, Pimenova, et al., 1995 | ALS |
ΔfH°liquid | -161.0 ± 1.3 | kJ/mol | Ccb | Parks, Manchester, et al., 1954 | ALS |
ΔfH°liquid | -174. | kJ/mol | Ccb | Landrieu, Baylocq, et al., 1929 | ALS |
ΔfH°liquid | -167. | kJ/mol | Ccb | Schmidlin, 1906 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -3743.0 ± 2.8 | kJ/mol | Ccr | Papina, Pimenova, et al., 1995 | Corresponding ΔfHºliquid = -154.9 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -3736.9 | kJ/mol | Ccb | Parks, Manchester, et al., 1954 | Corresponding ΔfHºliquid = -161.0 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -3723. | kJ/mol | Ccb | Landrieu, Baylocq, et al., 1929 | Corresponding ΔfHºliquid = -174. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -3724. | kJ/mol | Ccb | Barker, 1925 | Author was aware that data differs from previously reported values; Corresponding ΔfHºliquid = -174. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°liquid | -3731. | kJ/mol | Ccb | Schmidlin, 1906 | Corresponding ΔfHºliquid = -167. kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 216.7 | J/mol*K | N/A | Parks, Todd, et al., 1936 | Extrapolation below 90 K, 54.06 J/mol*K.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
223.6 | 307.5 | Griigo'ev, Yanin, et al., 1979 | T = 307 to 461 K. p = 0.98 bar.; DH |
215.94 | 298.15 | Nichols and Wads, 1975 | DH |
217.86 | 298.1 | Parks, Todd, et al., 1936 | T = 90 to 300 K.; DH |
215.9 | 298.5 | Smith and Andrews, 1931 | T = 102 to 299 K. Value is unsmoothed experimental datum.; DH |
220.5 | 298. | von Reis, 1881 | T = 290 to 485 K.; DH |
Reaction thermochemistry data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
By formula: C7H7O- + C7H8O = (C7H7O- • C7H8O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 125. ± 10. | kJ/mol | N/A | Caldwell, Rozeboom, et al., 1984 | gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M |
ΔrH° | 99.6 | kJ/mol | PHPMS | Caldwell and Kebarle, 1986 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 97.1 | J/mol*K | PHPMS | Caldwell and Kebarle, 1986 | gas phase; M |
ΔrS° | 123. | J/mol*K | N/A | Caldwell, Rozeboom, et al., 1984 | gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 86.6 ± 6.7 | kJ/mol | TDAs | Caldwell, Rozeboom, et al., 1984 | gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M |
By formula: C8H5- + C7H8O = (C8H5- • C7H8O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 111. ± 12. | kJ/mol | N/A | Caldwell, Rozeboom, et al., 1984 | gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 123. | J/mol*K | N/A | Caldwell, Rozeboom, et al., 1984 | gas phase; switching reaction(CH3O-)CH3OH, Entropy change calculated or estimated; re-evaluated using Meot-Ner(Mautner), 1986 and Paul and Kebarle, 1990; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 74.9 ± 8.4 | kJ/mol | IMRE | Caldwell, Rozeboom, et al., 1984 | gas phase; Reanchored to average data from Paul and Kebarle, 1990 and Meot-ner and Sieck, 1986.; value altered from reference due to change in acidity scale; B,M |
C7H7O- + =
By formula: C7H7O- + H+ = C7H8O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1548. ± 8.8 | kJ/mol | G+TS | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1520. ± 8.4 | kJ/mol | IMRE | Bartmess, Scott, et al., 1979 | gas phase; value altered from reference due to change in acidity scale; B |
By formula: C5H5- + C7H8O = (C5H5- • C7H8O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 80.3 ± 4.2 | kJ/mol | TDAs | Meot-ner, 1988 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 125. | J/mol*K | PHPMS | Meot-ner, 1988 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 43.1 ± 4.2 | kJ/mol | TDAs | Meot-ner, 1988 | gas phase; B |
By formula: F- + C7H8O = (F- • C7H8O)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 135.6 | kJ/mol | N/A | Mihalick, Gatev, et al., 1996 | gas phase; affinity derived using a ROH..F. neutral binding energy of 10.3 kcal/mol.; B |
By formula: C7H7I + H2O = HI + C7H8O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -12.6 | kJ/mol | Cm | Gellner and Skinner, 1949 | liquid phase; Heat of hydrolysis; ALS |
By formula: C7H7Br + H2O = HBr + C7H8O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -7.9 | kJ/mol | Cm | Gellner and Skinner, 1949 | liquid phase; Heat of hydrloysis; ALS |
By formula: C7H8O = C7H6O + H2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 53.93 | kJ/mol | Eqk | Cubberley and Mueller, 1946 | gas phase; ALS |
Henry's Law data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: Rolf Sander
Henry's Law constant (water solution)
kH(T) = k°H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
k°H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)
k°H (mol/(kg*bar)) | d(ln(kH))/d(1/T) (K) | Method | Reference | Comment |
---|---|---|---|---|
9000. | E | N/A | Value obtained by missing citation using the group contribution method. |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Papina, Pimenova, et al., 1995
Papina, T.S.; Pimenova, S.M.; Luk'yanova, V.A.; Kolesov, V.P.,
Standard enthalpies of formation of benzyl alcohol and α,α,α-trichlorotoluene,
Russ. J. Phys. Chem. (Engl. Transl.), 1995, 69, 1951-1953, In original 2148. [all data]
Parks, Manchester, et al., 1954
Parks, G.S.; Manchester, K.E.; Vaughan, L.M.,
Heats of combustion and formation of some alcohols, phenols, and ketones,
J. Chem. Phys., 1954, 22, 2089-2090. [all data]
Landrieu, Baylocq, et al., 1929
Landrieu, P.; Baylocq, F.; Johnson, J.R.,
Etude thermochimique dans la serie furanique,
Bull. Soc. Chim. France, 1929, 45, 36-49. [all data]
Schmidlin, 1906
Schmidlin, M.J.,
Recherches chimiques et thermochimiques sur la constitution des rosanilines,
Ann. Chim. Phys., 1906, 1, 195-256. [all data]
Barker, 1925
Barker, M.F.,
Calorific value and constitution,
J. Phys. Chem., 1925, 29, 1345-1363. [all data]
Parks, Todd, et al., 1936
Parks, G.S.; Todd, S.S.; Moore, W.A.,
Thermal data on organic compounds. XVI. Some heat capacity, entropy and free energy data for typical benzene derivatives and heterocyclic compounds,
J. Am. Chem. Soc., 1936, 58, 398-401. [all data]
Griigo'ev, Yanin, et al., 1979
Griigo'ev, B.A.; Yanin, G.S.; Rastorguev, Yu.L.; Thermophysical parameters of alcohols, Tr. GIAP,
54, 1979, 57-64. [all data]
Nichols and Wads, 1975
Nichols, N.; Wads, I.,
Thermochemistry of solutions of biochemical model compounds. 3. Some benzene derivatives in aqueous solution,
J. Chem. Thermodynam., 1975, 7, 329-336. [all data]
Smith and Andrews, 1931
Smith, R.H.; Andrews, D.H.,
Thermal energy studies. I. Phenyl derivatives of methane,
ethane and some related compounds. J. Am. Chem. Soc., 1931, 53, 3644-3660. [all data]
von Reis, 1881
von Reis, M.A.,
Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht,
Ann. Physik [3], 1881, 13, 447-464. [all data]
Caldwell, Rozeboom, et al., 1984
Caldwell, G.; Rozeboom, M.D.; Kiplinger, J.P.; Bartmess, J.E.,
Anion-alcohol hydrogen bond strengths in the gas phase,
J. Am. Chem. Soc., 1984, 106, 4660. [all data]
Paul and Kebarle, 1990
Paul, G.J.C.; Kebarle, P.,
Thermodynamics of the Association Reactions OH- - H2O = HOHOH- and CH3O- - CH3OH = CH3OHOCH3- in the Gas Phase,
J. Phys. Chem., 1990, 94, 12, 5184, https://doi.org/10.1021/j100375a076
. [all data]
Meot-ner and Sieck, 1986
Meot-ner, M.; Sieck, L.W.,
Relative acidities of water and methanol, and the stabilities of the dimer adducts,
J. Phys. Chem., 1986, 90, 6687. [all data]
Caldwell and Kebarle, 1986
Caldwell, G.; Kebarle, P.,
Mobility of Gaseous Ions in Weak Electric Fields
in Unpublished results, 1986. [all data]
Meot-Ner(Mautner), 1986
Meot-Ner(Mautner), M.,
Comparative Stabilities of Cationic and Anionic Hydrogen-Bonded Networks. Mixed Clusters of Water-Methanol,
J. Am. Chem. Soc., 1986, 108, 20, 6189, https://doi.org/10.1021/ja00280a014
. [all data]
Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr.,
The gas phase acidity scale from methanol to phenol,
J. Am. Chem. Soc., 1979, 101, 6047. [all data]
Meot-ner, 1988
Meot-ner, M.,
The Ionic Hydrogen Bond and Solvation. 7. Interaction Energies of Carbanions with Solvent Molecules,
J. Am. Chem. Soc., 1988, 110, 12, 3858, https://doi.org/10.1021/ja00220a022
. [all data]
Mihalick, Gatev, et al., 1996
Mihalick, J.E.; Gatev, G.G.; Brauman, J.I.,
Electron Photodetachment Spectroscopy of Solvated Anions: RO.HF- or ROH.F-?,
J. Am. Chem. Soc., 1996, 118, 49, 12424, https://doi.org/10.1021/ja954202k
. [all data]
Gellner and Skinner, 1949
Gellner, O.H.; Skinner, H.A.,
Dissociation energies of carbon-halogen bonds. The bond strengths allyl-X and benzyl-X,
J. Chem. Soc., 1949, 1145-1148. [all data]
Cubberley and Mueller, 1946
Cubberley, A.H.; Mueller, M.B.,
Equilibrium studies on the dehydrogenation of primary and secondary alcohols. I. 2-Butanol, 2-octanol, cyclopentanol and benzyl alcohol,
J. Am. Chem. Soc., 1946, 68, 1149-1151. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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